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Check availability on Chestertown Gay-Friendly Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Chestertown LGBT-friendly hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
₹9,881
₹10,968 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
₹6,882
₹7,639 total
includes taxes & fees
1 Oct - 2 Oct
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Jane
₹10,341
₹11,822 total
includes taxes & fees
27 Sept - 28 Sept
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
₹9,862
₹10,947 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
₹8,152
₹9,131 total
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
A patio with outdoor seating, overlooking a marina with boats.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
An indoor swimming pool with clear views of boats and water.

6. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
₹14,031
₹15,575 total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Kent Island Marina
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
Canada
michelle
₹11,698
₹13,102 total
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Bel Air
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A modern restaurant with a bar area, seating, and a counter with a menu display.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.

8. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Adam
₹9,328
₹10,447 total
includes taxes & fees
4 Oct - 5 Oct
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
A hotel room with a dining area, a TV, a dresser, and a tray table.
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.

9. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
₹10,128
₹11,343 total
includes taxes & fees
30 Sept - 1 Oct
Homewood Suites by Hilton Bel Air
A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.
A hotel room with a large bed, a desk with a television, a chair, and a nightstand with a lamp.
A hotel entrance with a covered parking area, a clear sign indicating 'Clearance 14' and 'Welcome' sign above the entrance.
A gym with treadmills, elliptical machines, and a stationary bike.

10. Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
Aberdeen
United States
Miguel
₹10,912
₹12,222 total
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn & Suites Baltimore/Aberdeen
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Top Chestertown Hotel Reviews

Frequently asked questions

Searching for an LGBTQ-friendly hotel in Chestertown?
Whether you are travelling with your partner or flying solo, you'll find Chestertown hotels that are members of the International Gay & Lesbian Travel Association on Expedia. Discover the people, places and traditions found only in Chestertown.
What is the top LGBTQ-friendly place to stay in Chestertown?
The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown are other good options for your stay.
How many LGBTQ-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly hotels in Chestertown.
What should I do while I'm visiting Chestertown?
During your trip, get out and enjoy everything Chestertown has to offer. You and your travelling companions may want to visit Historical Society of Kent County Maryland, Chestertown Historic District and Rolphs Wharf Marina. While you're here, create some great memories of your trip with stops at Northern Chesapeake Bay, Chesapeake Bay and Garfield Center for the Arts at the Prince Theater.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Chestertown, hotels affiliated with IGLTA prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Chestertown?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Chestertown, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.

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